Science Faculty

Enantioselective Synthesis of 4-Isoxazolines by 1,3-Dipolar Cycloadditions of Nitrones to Alkynals Catalyzed by Fluorodiphenylmethylpyrrolidines

Author/s

Alemán, J.; Fraile, A.; Marzo, L.; García Ruano, J. L.; Izquierdo, C.; Díaz-Tendero, S.

Año de edición

2012

Referencia completa

Adv. Synth. Catal. 2012, 354, 1665-1671. DOI: 10.1002/adsc.201200033

Resumen

The first organocatalytic enantioselective 1,3-dipolar reaction between nitrones and alkynals catalyzed by (S)-2-(fluorodiphenylmethyl)pyrrolidine to give 4-isoxazolines (2,3-dihydroisoxazoles) with high enantiomeric excess, excellent yields and low catalyst loading (1–5 mol%) is presented. The catalytic loading could be reduced to 1 mol% with
only slight increases in reaction times.